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Wiley, Angewandte Chemie, 39(124), p. 10024-10028, 2012

DOI: 10.1002/ange.201205233

Wiley, Angewandte Chemie International Edition, 39(51), p. 9886-9890, 2012

DOI: 10.1002/anie.201205233

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Synthesis of Enantiomerically Enriched Imidazolidin-2-Ones through Asymmetric Palladium-Catalyzed Alkene Carboamination Reactions

Journal article published in 2012 by Brett A. Hopkins, John P. Wolfe ORCID
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This paper is available in a repository.

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Abstract

A catalyst composed of Pd2(dba)3 and (S)-Siphos-PE is effective for the enantioselective coupling of N-allyureas with aryl bromides to afford 4-substituted imidazolidin-2-ones with up to 95% ee. Added water leads to significantly improved enantioselectivities with electron-poor aryl halide substrates. The mechanism of these transformations is discussed, and evidence is presented which suggests that, in contrast to other asymmetric alkene carboaminations, C–C bond-forming reductive elimination is the enantiodetermining step of these reactions.